Sodium sulfate decahydrate → HCID 57786020, 화합물

HRID 1399263노트

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HRID 1399263 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:31](OC)=[O:32])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:26]([Cl:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[Cl:30])[CH2:18][CH2:19][CH2:20][N:13]21.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1.C(#N)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:31]=[O:32])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:22]([Cl:30])=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[Cl:27])[CH2:18][CH2:19][CH2:20][N:13]21

참가 물질

10

반응물 4

HCID 62649Sodium sulfate decahydrateHCID 159087TriacetoxyperiodinaneHCID 21226445Aluminium lithium hydrideHCID 57786371HCID 57786371, 화합물

생성물 1

HCID 57786020HCID 57786020, 화합물수율 89%

시약·촉매·용매 5

HCID 679Dimethyl Sulfoxide용매HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a suspension of lithium aluminum hydride (45.7 mg, 1.20 mmol) in tetrahydrofuran (4 mL) was added a solution of methyl 9-chloro-1-(2,6-dichloro-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (177 mg, 0.401 mmol) in tetrahydrofuran (4 mL) at 0° C., and the resultant mixture was stirred at 0° C. for 5 min. After sodium sulfate decahydrate (450 mg) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo to give a crude solid. To a solution of the crude solid in acetonitrile (4 mL) and dimethylsulfoxide (0.8 mL) was added Dess-Martin reagent (204 mg, 0.481 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 20 min, diluted with aqueous sodium bicarbonate and ethyl acetate, filtered and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (146 mg, 0.356 mmol, 89%).

후처리

  1. filtrationthe resultant mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give a crude solid
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-ce1b12482a434c3d988f605fe80f1a57
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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